Combating pests with N-acetyl-0-(2-chloro-1-fluoro-ethyl)-thionophosphoric (phosphonic) acid ester-amides

ABSTRACT

N-Acetyl-0-(2-chloro-1-fluoro-ethyl)-thionophosphoric (phosphonic) acid ester-amides of the formula ##STR1## IN WHICH R is alkyl or alkoxy, which possess arthropodicidal and nematicidal properties.

The present invention relates to and has for its objects the provisionof particular new N-acetyl-O-(2-chloro-1-fluoroethyl)-thionophosphoric(phosphonic) acid ester-amides which possess arthropodicidal andnematicidal properties, active compositions in the form of mixtures ofsuch compounds with solid and liquid dispersible carrier vehicles, andmethods for producing such compounds and for using such compounds in anew way especially for combating pests, e.g. insects, acarids andnematodes, with other and further objects becoming apparent from a studyof the within specification and accompanying examples.

It is already known that certain chlorine-substituted alkyl-phosphonicacid esters, for exampleO,O-dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonic acid ester, aredistinguished by an insecticidal and acaricidal activity (see U.S. Pat.No. 2,701,225).

The present invention now provides, as new compounds, theN-acetyl-O-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric (phosphonic) acidester-amides of the general formula ##STR2## in which R represents alkylor alkoxy,

Preferably, R represents straight-chain or branched alkyl with 1 to 6(especially 1 to 3) carbon atoms or straight-chain or branched alkoxywith 1 to 6 (especially 1 to 3) carbon atoms.

Surprisingly, theN-acetyl-O-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric(phosphonic) acidester-amides according to the invention exhibit a better insecticidal,acaricidal and nematicidal action than the correspondingchlorine-substituted alkylphosphonic acid esters of analogous structureand the same type of action. The products according to the presentinvention thus represent a true enrichment of the art.

The invention also provides a process for the preparation of anN-acetyl-O-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric (phosphonic) acidester-amide of the formula (I), in which anO-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric(phosphonic) acidester-amide of the general formula ##STR3## in which R has the meaningstated above, is reacted with acetic anhydride, optionally in thepresence of a solvent or diluent and optionally in the presence of anacid catalyst.

If, for example,O-iso-propyl-O-(2-chloro-1-fluoroethyl)-thionophosphoric aciddiester-amide and acetic anhydride are used as the starting materials,the course of the reaction can be represented by the following equation:##STR4##

The O-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric (phosphonic) acidester-amides of the formula (II) to be used as starting materials aredisclosed in U.S. Application Ser. No. 806,888, filed June 15, 977, nowpending, and can be prepared by reactingO-(2-chloro-1-fluoro-ethyl)-thiono-phosphoric(phosphonic) acid esterhalides of the general formula ##STR5## in which Hal represents halogen,preferably chlorine, and

R has the meaning stated above, with ammonia, optionally in the presenceof a solvent.

Examples of starting materials of the formula (II) which may bementioned are: methane-, ethane- and n- oriso-propane-O-(2-chloro-1-fluoro-ethyl)-thionophosphonic acidester-amide, and O-methyl-, O-ethyl- and O-n- or-iso-propyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric aciddiester-amide.

The O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid diester halidesused as starting materials for the preparation of the compounds of theformula (II) can be prepared in a manner which is in itself known byreacting O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid esterdichloride with the corresponding alcohols.

The O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid ester dihalides tobe used as starting materials and theO-(2-chloro-1-fluoro-ethyl)-thionophosphonic acid ester mono-halides canbe obtained from the corresponding P=O compounds with alkane- oraryl-dithiophosphonic acid anhydrides, optionally mixed with phosphorussulphochloride and optionally in the presence of a solvent, according tothe following equation: ##STR6## wherein Hal has the meaning statedabove,

R¹ represents Hal or alkyl and

R² represents alkyl or aryl.

Examples of the O-(2-chloro-1-fluoroethyl)-thionophosphoric acid esterdihalides and -thionophosphonic acid ester monohalides which may bementioned are: methane-, ethane-, n-propane- andiso-propane-O-(2-chloro-1-fluoro-ethyl)-thionophosphonic acid esterchloride and O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid esterdichloride.

The O-(2-chloro-1-fluoro-ethyl)-phosphonic acid ester halides to be usedhere as starting materials and theO-(2-chloro-1-fluoro-ethyl)-phosphonic acid ester dihalides andO-alkyl-O-(2-chloro-1-fluoro-ethyl)-phosphoric acid diester halides canbe prepared by a process which does not belong to the state of the art,by reacting a phosphoric (or phosphonic) acid ester and vinyl fluoride,simultaneously using a chlorinating agent, such as chlorine, attemperatures between -50° and +120° C., optionally in the presence of aFriedel-Crafts catalyst and optionally in the presence of a solvent, togive the corresponding O-(1-fluoro-2-chloroethyl)-phosphoric(phosphonic)acid ester halides, according to the following equation: ##STR7##wherein Hal has the meaning stated above,

R³ represents alkyl, alkoxy or Hal and

R° represents alkyl.

Examples of the O-(2-chloro-1-fluoro-ethyl)-phosphonic acid esterhalides, O-(2-chloro-1-fluoro-ethyl)-phosphoric acid ester halides andO-alkyl-O-(2-chloro-1-fluoro-ethyl)-phosphoric acid diester halideswhich may be mentioned are: methane-, ethane-, n-propane- andiso-propane-O-(2-chloro-1-fluoro-ethyl)-phosphonic acid ester chloride,O-(2-chloro-1-fluoro-ethyl)-phosphoric acid ester dichloride andO-methyl-, O-ethyl-, O-n-propyl- andO-iso-propyl-O-(2-chloro-1-fluoro-ethyl)-phosphoric acid diesterchloride.

The acetic anhydride which is also to be used as a starting material forthe preparation of the compounds of the formula (I) is known.

The process for the preparation of the compounds according to theinvention is preferably carried out also using a suitable solvent ordiluent. Possible solvents or diluents are virtually all the inertorganic solvents, especially aliphatic and aromatic, optionallychorinated hydrocarbons, such as benzene, toluene, xylene, benzine,methylene chloride, chloroform, carbon tetrachloride or chlorobenzene;ethers, for example diethyl ether, dibutyl ether and dioxane ketones,for example acetone, methyl ethyl ketone, methyl isopropyl ketone andmethyl isobutyl ketone; and nitriles, such as acetonitrile andpropionitrile. The starting material acetic anhydride can, however, beemployed in excess and thus simultaneously serves as reactant andsolvent. A few drops of sulphuric acid are preferably added as thecatalyst.

The reaction temperature can be varied within a relatively wide range.In general, the reaction is carried out at from 30° to 100° C.,preferably at from 45° to 75° C.

In general, the reaction is allowed to proceed under normal pressure.

For carrying out the reaction, both the reactants are introduced into areaction vessel, the acetic anhydride preferably being employed inexcess, and, after adding an acid catalyst, for example sulphuric acid,whereupon in exothermic reaction occurs, the mixture is subsequentlyreacted for a few hours. Thereafter, the reaction solution is taken upin an organic solvent and the organic phase is worked up in thecustomary manner by washing and drying and distilling off the solvent.

The new compounds are obtained in the form of oils, some of which cannotbe distilled without decomposition, but can be freed from the lastvolatile constituents by so-called "incipient distillation", that is tosay by prolonged heating to moderately elevated temperatures underreduced pressure, and can be purified in this manner. The refractiveindex is used for their characterization.

The active compounds are well tolerated by plants, have a favorablelevel of toxicity to warm-blooded animals, and can be used for combatingarthropod pests, especially insects and acarids, and nematode pestswhich are encountered in agriculture, in forestry, in the protection ofstored products and of materials, and in the hygiene field. They areactive against normally sensitive and resistant species and against allor some stages of development. The abovementioned pests include:

from the class of the Isopoda, for example Oniscus asellus,Armadillidium vulgare and Porcellio scaber;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Chilopoda, for example Geophilus carpophagus andScutigera spec.;

from the class of the Symphyla, for example Scutigerella immaculata;

from the order of the Thysanura, for example Lepisma saccharina;

from the order of the Collembola, for example Onychiurus armatus;

from the order of the Orthoptera, for example Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria;

from the order of the Dermaptera, for example Forficula auricularia;

from the order of the Isoptera, for example Reticulitermes spp.;

from the order of the Anoplura, for example Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.;

from the order of the Mallophaga, for example Trichodectes spp. andDamalinea spp.;

from the order of the Thysanoptera, for example Hercinothrips femoralisand Thrips tabaci;

from the order of the Heteroptera, for example Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.;

from the order of the Homoptera, for example Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.;

from the order of the Lepidoptera, for example Pectinophora gossypiella,Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella,Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria,Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella,Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Eariasinsulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolisflammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsapomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestiakeuhniella, Galleria mellonella, Cacoecia podana, Capua reticulana,Choristoneura fumiferana, Clysia ambiguella, Homona magnanima andTortrix viridana;

from the order of the Coleoptera, for example Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhyncchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica;

from the order of the Hymenoptera, for example Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharanois and Vespa spp.;

from the order of the Diptera, for example Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa;

from the order of the Siphonaptera, for example Xenopsylla cheopis andCeratophyllus spp.;

from the class of the Arachnida, for example Scorpio maurus andLatrodectus mactans;

from the order of the Acarina, for example Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Ripicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The plant-parasitic nematodes include Pratylenchus spp., Radopholussimilis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heteroderaspp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinemaspp., and Trichodorus spp.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, foams, pastes, soluble powders, granules, aerosols,suspension-emulsion concentrates, seed-treatment powders, natural andsynthetic materials impregnated with active compound, very fine capsulesin polymeric substances, coating compositions for use on seed, andformulations used with burning equipment, such as fumigating cartridges,fumigating cans and fumigating coils, as well as ULV cold mist and warmmist formulations.

These formulations may be produced in known manner, for example bymixing the active compounds with extenders, that is to say liquid orliquefied gaseous or solid diluents or carriers, optionally with the useof surfaceactive agents, that is to say emulsifying agents and/ordispersing agents and/or foam-forming agents. In the case of the use ofwater as an extender, organic solvents can, for example, also be used asauxiliary solvents.

As liquid solvents diluents or carriers, especially solvents, there aresuitable in the main, aromatic hydrocarbons, such as xylene, toluene oralkyl naphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane orparaffins, for example mineral oil fractions, alcohols, such as butanolor glycol as well as their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, orstrongly polar solvents, such as dimethylformamide anddimethylsulphoxide, as well as water.

By liquefied gaseous diluents or carriers are meant liquids which wouldbe gaseous at normal temperature and under normal pressure, for exampleaerosol propellants, such as halogenated hydrocarbons as well as butane,propane, nitrogen and carbon dioxide.

As solid carriers there may be used ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such ashighly-dispersed silicic acid, alumina and silicates. As solid carriersfor granules there may be used crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, as well assynthetic granules or inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, corn cobs and tobaccostalks.

As emulsifying and/or foam-forming agents there may be used non-ionicand anionic emulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycolethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well asalbumin hydrolysis products. Dispersing agents include, for example,lignin sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, can be used in theformulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs or metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain from 0.1 to 95 percent by weight ofactive compound, preferably from 0.5 to 90 percent by weight.

The active compounds according to the invention may be used in the formof their formulations of the types that are commercially available or inthe use forms prepared from these formulations.

The active compound content of the use forms prepared from theformulations of the types that are commercially available can varywithin wide ranges. The active compound concentration of the use formscan be from 0.0000001 to 100% by weight of active compound, preferablyfrom 0.01 to 10% by weight.

The compounds may be employed in a customary manner appropriate for theparticular use forms.

When used against pests harmful to health and pests of stored products,the active compounds are distinguished by an excellent residual activityon wood and clay as well as a good stability to alkali on limedsubstrates.

The compounds according to the present invention can also be used in thefield of veterinary medicine, since they are also active against animalparasites.

In the veterinary field, the active compounds according to the inventionmay be used in a known manner, such as orally in the form of, forexample, tablets, capsules, drenches and granules; dermally by means of,for example, dipping, spraying, pouring-on, spotting-on and powdering;and parenterally, for example by means of injections.

The present invention also provides an arthropodicidal or nematicidalcomposition containing as active ingredient a compound of the presentinvention in admixture with a solid or liquefied gaseous diluent orcarrier or in admixture with a liquid diluent or carrier containing asurface-active agent.

The present invention also provides a method of combating arthropods(especially insects or acarids) or nematodes which comprises applying tothe arthropods or nematodes, or to a habitat thereof, a compound of thepresent invention alone or in the form of a composition containing asactive ingredient a compound of the present invention in admixture witha diluent or carrier.

The present invention also provides a method of freeing or protectingdomesticated animals from ectoparasitical insects or acarids whichcomprises applying to said animals a compound according to the presentinvention, in admixture with a diluent or carrier.

The present invention further provides crops protected from damage byarthropods or nematodes by being grown in areas in which immediatelyprior to and/or during the time of the growing a compound of the presentinvention was applied alone or in admixture with a diluent or carrier.

It will be seen that the usual methods of providing a harvested crop maybe improved by the present invention.

The present invention further provides domesticated animals wheneverfreed or protected from ectoparasitical insects and acarids by theapplication to said animals of a compound according to the presentinvention, in admixture with a diluent or carrier.

The preparation of the novel compounds is shown in the followingillustrative examples:

EXAMPLE 1 ##STR8##

A slurry of 150 ml of toluene, 96 g (0.4 mol) of anisyldithiophosphoricacid anhydride and 84 g (0.4 mol) ofO-(2-chloro-1-fluoro-ethyl)-ethane-phosphonic acid ester chloride washeated to 115°-120° C. for 2 hours, cooled and poured into 1 liter ofligroin. The mixture was filtered over kieselguhr, the solvent wasevaporated off from the filtrate and the residue was distilled. 33 g(73% of theory) of O-(2-chloro-1-fluoro-ethyl)-thionoethane-phosphonicacid ester chloride with a boiling point of 82° C./2 mm Hg wereobtained. ##STR9##

Ammonia was passed over a solution of 67.5 g (0.3 mol) of theO-(2-chloro-1-fluoro-ethyl)-thionoethanephosphonic acid ester chloride,prepared under (a), in 300 ml of acetonitrile, while stirring. The endof the reaction was recognized by the fact that the reaction mixtureremained alkaline even after the stream of ammonia had been shut off.The reaction mixture was taken up in 500 ml of toluene and the organicphase was washed several times with water, dried over sodium sulphateand filtered. The toluene was distilled off in vacuo and the residue wassubjected to incipient distillation using a mercury pump. 51 g (83% oftheory) of O-(2-chloro-1-fluoro-ethyl)thionoethanephosphonic acidester-amide having a refractive index n_(D) ²⁴ of 1.5111 were obtained.##STR10##

2 drops of pure, concentrated sulphuric acid were added to the mixtureof 21 g (0.1 mol) of O-(2-chloro-1-fluoro-ethyl)-thionoethanephosphonicacid ester-amide and 11 g of acetic anhydride, whereupon the temperaturerose to 55° C. The reaction mixture was left to stand overnight andtaken up in toluene and the organic phase was washed with a bicarbonatesolution until neutral. After drying the organic phase, the toluene wasstripped off in vacuo and the residue was subjected to incipientdistillation using a mercury pump. 18 g (73% of theory) ofO-(2-chloro-1-fluoro-ethyl)-N-acetylthionoethanephosphonic acidesteramide having a refractive index n_(D) ²⁴ of 1.5080 were obtained.

EXAMPLE 2: ##STR11##

A mixture of 17 g of phosphorus sulphochloride, 12 g (0.05 mol) ofO-(2-chloro-1-fluoro-ethyl)-phosphoric acid ester dichloride and 3 g ofmethanedithiophosphonic acid anhydride was heated to a temperature of150° C. (externally) for 15 hours, cooled and diluted with 200 ml ofligroin. The mixture was filtered over kieselguhr, the solvent wasevaporated off from the filtrate in vacuo and the residue was distilled.7 g (61% of theory) of O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acidester dichloride, which was 90% pure according to the gas chromatogramand had a boiling point of 65° C./3 mm Hg, were obtained. ##STR12##

0.2 mol of sodium methylate in solution was added to a solution of 47 g(0.2 mol) of O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid esterdichloride in 300 ml of toluene, while cooling. The mixture wassubsequently stirred at a temperature up to 10° C. for 30 minutes andwashed twice with water. The organic layer was dried over sodiumsulphate, the toluene was evaporated off under reduced pressure and theresidue was distilled.O-Methyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid diesterchloride with a boiling point of 38°-42° C./0.01 mm Hg was obtained in81% yield. ##STR13##

Ammonia was passed into a solution of 23 g (0.1 mol) ofO-methyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid diesterchloride in 200 ml of acetonitrile at +20° C. until the reaction hadended. The reaction mixture was poured into water and the resultingmixture was taken up in toluene, the organic phase was washed with waterand dried over sodium sulphate, the toluene was evaporated off and theresidue was distilled under greatly reduced pressure. 16 g (77% oftheory) of O-methyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric aciddiester-amide having a refractive index n_(D) ²³ of 1.4930 wereobtained. ##STR14##

0.5 ml of pure, concentrated sulphuric acid was added to a solution of20 ml of toluene, 21 g (0.1 mol) ofO-methyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric acid diester-amideand 11 g of acetic anhydride, while stirring, whereupon the temperaturerose to 55° C. The reaction mixture was left to stand overnight andtaken up in toluene and the organic phase was washed with a bicarbonatesolution until neutral. After drying over sodium sulphate, the organicphase was filtered, the toluene was stripped off in vacuo and theresidue was subjected to incipient distillation using a mercury pump. 16g (64% of theory) ofO-methyl-O-(2-chloro-1-fluoro-ethyl)-N-acetyl-thionophosphoric aciddiester-amide having a refractive index of n_(D) ²⁴ of 1.4959 wereobtained.

The insecticidal, acaricidal and nematicidal activity of the compoundsof this invention is illustrated by the following biotest Examples.

EXAMPLE 3

Myzus test (contact action)

Solvent: 3 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound was mixed with the stated amount of solventcontaining the stated amount of emulsifier and the concentrate wasdiluted with water to the desired concentration.

Cabbage plants (Brassica oleracea) which had been heavily infested withpeach aphids (Myzus persicae) were sprayed with the preparation of theactive compound until dripping wet.

After the specified periods of time, the degree of destruction wasdetermined and the compound of Example 1 showed a good activity.

EXAMPLE 4

Tetranychus test (resistant)

Solvent: 3 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound was mixed with the stated amount of solvent andthe stated amount of emulsifier and the concentrate was diluted withwater to the desired concentration.

Bean plants (Phaseolus vulgaris) which were heavily infested with thetwo-spotted spider mite (Tetranychus urticae) in all stages ofdevelopment were sprayed with the preparation of the active compounduntil dripping wet.

After the specified periods of time, the degree of destruction wasdetermined and the compound of Example 2 showed a good activity.

EXAMPLE 5

Critical concentration test/nematodes

Test nematode: Meloidogyne incognita

Solvent: 3 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound was mixed with the stated amount of solvent, thestated amount of emulsifier was added and the concentrate was dilutedwith water to the desired concentration.

The preparation of active compound was intimately mixed with soil whichwas heavily infested with the test nematodes. The concentration of theactive compound in the preparation was of practically no importance;only the amount of active compound per unit volume of soil, which isgiven hereinafter in ppm (=mg/l), was decisive. The treated soil wasfilled into pots, lettuce was sown in and the pots were kept at agreenhouse temperature of 27° C.

After 4 weeks, the lettuce roots were examined for infestation withnematodes (root galls), and the degree of effectiveness of the activecompound was determined.

In this test, for example, the compound of Example 1 showed a goodactivity.

EXAMPLE 6

Test with parasitic fly larvae

Emulsifier: 80 parts by weight of nonylphenol polyglycol ether

To produce a suitable preparation of active compound, 20 parts by weightof the active compound in question were mixed with the stated amount ofthe emulsifier and the mixture thus obtained was diluted with water tothe desired concentration.

About 20 fly larvae (Lucilia cuprina) were introduced into a test tubewhich contained approx. 2 ml of horse muscle. 0.5 ml of the preparationof active compound was applied to this horse meat. After 24 hours, thedegree of destruction was determined.

In this test, for example, the compound of Example 2 showed a goodactivity.

It will be appreciated that the instant specification and examples areset forth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

What we claim is:
 1. AnN-acetyl-O-(2-chloro-1-fluoro-ethyl)-thionophosphoric (phosphonic) acidester-amide of the formula ##STR15## in which R is alkyl or alkoxy.
 2. Amethod of combating arthropods or nematodes which comprises applying tothe arthropods or nematodes, or to a habitat thereof, anarthropodicidally or nematicidally effective amount of a compoundaccording to claim
 1. 3. A compound according to claim 1, in which R isalkyl with 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms.
 4. Acompound according to claim 1 wherein such compound isO-(2-chloro-1-fluoro-ethyl)-N-acetylthionoethanephosphonic acidester-amide of the formula ##STR16##
 5. A compound according to claim 1,wherein such compound isO-methyl-O-(2-chloro-1-fluoro-ethyl)-N-acetyl-thionophosphoric aciddiester-amide of the formula ##STR17##
 6. An arthropodicidal ornematicidal composition containing as active ingredient anarthropodicidally or nematicidally effective amount of a compoundaccording to claim 1 in admixture with a diluent.
 7. The methodaccording to claim 2, wherein the compound is applied to a domesticatedanimal, thereby to protect the animal from ectoparasitical insects andacarids, and said compound isO-(2-chloro-1-fluoro-ethyl)-N-acetylthionoethanephosphonic acidester-amide.
 8. The method according to claim 2, wherein the compound isapplied to a domesticated animal, thereby to protect the animal fromectoparasitical insects and acarids, and said compound isO-methyl-O-(2-chloro-1-fluoro-ethyl)-N-acetyl-thionophosphoric aciddiester-amide.